KEGG   PATHWAY: ko00998
Entry
ko00998                     Pathway                                
Name
Biosynthesis of various antibiotics
  Including
Kanosamine biosynthesis, Aurachin biosynthesis, Bacilysin biosynthesis, Puromycin biosynthesis, Dapdiamides biosynthesis, Fosfomycin biosynthesis, Cremeomycin biosynthesis, Fumagillin biosynthesis, Pentalenolactone biosynthesis, Terpentecin biosynthesis, Roseoflavin biosynthesis, Cycloserine biosynthesis
Class
Metabolism; Biosynthesis of other secondary metabolites
Pathway map
ko00998  Biosynthesis of various antibiotics
ko00998

Module
M00785  Cycloserine biosynthesis, arginine/serine => cycloserine [PATH:ko00998]
M00787  Bacilysin biosynthesis, prephenate => bacilysin [PATH:ko00998]
M00788  Terpentecin biosynthesis, GGAP => terpentecin [PATH:ko00998]
M00819  Pentalenolactone biosynthesis, farnesyl-PP => pentalenolactone [PATH:ko00998]
M00848  Aurachin biosynthesis, anthranilate => aurachin A [PATH:ko00998]
M00877  Kanosamine biosynthesis, glucose 6-phosphate => kanosamine [PATH:ko00998]
M00889  Puromycin biosynthesis, ATP => puromycin [PATH:ko00998]
M00890  Roseoflavin biosynthesis, FMN => roseoflavin [PATH:ko00998]
M00903  Fosfomycin biosynthesis, phosphoenolpyruvate => fosfomycin [PATH:ko00998]
M00904  Dapdiamides biosynthesis, L-2,3-diaminopropanoate => dapdiamide A/B/C [PATH:ko00998]
M00951  Cremeomycin biosynthesis, aspartate/3,4-AHBA => cremeomycin [PATH:ko00998]
M00969  Fumagillin biosynthesis, farnesyl-PP => fumagillin [PATH:ko00998]
Drug
D05653  Puromycin (USAN)
Orthology
K01841  pepM; phosphoenolpyruvate phosphomutase [EC:5.4.2.9]
K01957  ddaH; N-3-fumaroyl-(S)-2,3-diaminopropanoate amidotransferase
K02078  acpP, acpM; acyl carrier protein
K09459  E4.1.1.82; phosphonopyruvate decarboxylase [EC:4.1.1.82]
K09460  auaEII; anthranilate-CoA ligase [EC:6.2.1.32]
K12250  ptlA; pentalenene synthase [EC:4.2.3.7]
K12628  pur10; puromycin biosynthesis protein Pur10 [EC:1.-.-.-]
K12629  pur7; puromycin biosynthesis protein Pur7 [EC:3.-.-.-]
K12630  pur4; puromycin biosynthesis protein Pur4 [EC:2.-.-.-]
K12631  pur6; puromycin biosynthesis protein Pur6
K12632  pac; puromycin N-acetyltransferase [EC:2.3.-.-]
K12633  pur5; N-methyl-transferase [EC:2.1.1.-]
K12634  pur3; puromycin biosynthesis protein Pur3
K12635  dmpM; O-demethylpuromycin O-methyltransferase [EC:2.1.1.38]
K12636  napH; N-acetylpuromycin N-acetylhydrolase
K12901  fomC; phosphonoacetaldehyde reductase
K12902  fom3; phosphonoacetaldehyde methylase [EC:2.1.1.308]
K12903  fom4; (S)-2-hydroxypropylphosphonic acid epoxidase [EC:1.11.1.23]
K12904  phpC; phosphonoacetaldehyde reductase [EC:1.1.1.309]
K13037  bacD; L-alanine-L-anticapsin ligase [EC:6.3.2.49]
K14245  auaC; PKS ketosynthase (KS/KS alpha) [EC:2.3.1.-]
K14246  auaD; PKS chain-length factor (CLF/KS beta) [EC:2.3.1.-]
K15907  ptlI, CYP183A; pentalenene oxygenase [EC:1.14.15.32]
K17476  penM, pntM, CYP161C; pentalenolactone synthase [EC:1.14.19.8]
K17747  ptlF; 1-deoxy-11beta-hydroxypentalenate dehydrogenase [EC:1.1.1.340]
K17876  CYP105D; pentalenic acid synthase [EC:1.14.15.11]
K18056  pntH, ptlH; 1-deoxypentalenic acid 11beta-hydroxylase [EC:1.14.11.35]
K18057  pntD, penD, ptlD; pentalenolactone F synthase [EC:1.14.11.36]
K18091  pntE, penE, ptlE; pentalenolactone D synthase [EC:1.14.13.170 1.14.13.171]
K18652  ntdC; glucose-6-phosphate 3-dehydrogenase [EC:1.1.1.361]
K18653  ntdA; 3-dehydro-glucose-6-phosphate---glutamate transaminase [EC:2.6.1.104]
K18654  ntdB; kanosamine-6-phosphate phosphatase [EC:3.1.3.92]
K19546  bacA; prephenate decarboxylase [EC:4.1.1.100]
K19547  bacB; 3-[(4R)-4-hydroxycyclohexa-1,5-dien-1-yl]-2-oxopropanoate isomerase [EC:5.3.3.19]
K19548  bacC; dihydroanticapsin dehydrogenase [EC:1.1.1.385]
K19549  bacF; bacilysin biosynthesis transaminase BacF [EC:2.6.1.-]
K19550  bacG; bacilysin biosynthesis oxidoreductase BacG [EC:1.3.1.-]
K19723  dcsB; Nomega-hydroxy-L-arginine amidinohydrolase [EC:3.5.3.25]
K19724  dcsC; O-ureido-serine racemase [EC:5.1.1.19]
K19725  dcsD; O-ureido-L-serine/cysteine synthase [EC:2.6.99.3 2.5.1.47]
K19726  dcsE; serine/homoserine O-acetyltransferase [EC:2.3.1.30 2.3.1.31]
K19727  dcsG; O-ureido-D-serine cyclo-ligase [EC:6.3.3.5]
K19741  dcsA; Nomega-hydroxy-L-arginine synthase [EC:1.14.-.-]
K19834  cyc2; terpentetriene synthase [EC:4.2.3.36]
K19835  cyc1; terpentedienyl-diphosphate synthase [EC:5.5.1.15]
K21271  auaH; aurachin B dehydrogenase [EC:1.1.1.394]
K21272  auaG; aurachin C monooxygenase/isomerase [EC:1.14.13.222]
K21295  AF510; 5-dehydro-6-demethoxyfumagillol synthase [EC:1.14.14.184]
K21721  sbnB; N-[(2S)-2-amino-2-carboxyethyl]-L-glutamate dehydrogenase [EC:1.5.1.51]
K21949  sbnA; N-(2-amino-2-carboxyethyl)-L-glutamate synthase [EC:2.5.1.140]
K22113  ddaG; fumarate---(S)-2,3-diaminopropanoate ligase [EC:6.3.2.46]
K22114  ddaF; dapdiamide synthase [EC:6.3.2.47]
K22269  rosA; 8-amino-8-demethylriboflavin N,N-dimethyltransferase [EC:2.1.1.343]
K22392  hppE; (S)-2-hydroxypropylphosphonic acid epoxidase [EC:1.11.1.23]
K22569  AF520; (+)-exo-beta-bergamotene synthase [EC:4.2.3.211]
K22570  AF480; 5-dehydro-6-demethoxyfumagillol dioxygenase [EC:1.14.11.82]
K22571  AF390-400, fmaD; 5-dehydro-6-demethoxy-6-hydroxyfumagillol O-methyltransferase [EC:2.1.1.387]
K22572  AF490; 5-dehydrofumagillol 5-reductase [EC:1.1.1.437]
K22573  AF370; fumagillin biosynthesis polyketide synthase
K22574  AF380; fumagillin biosynthesis transferase
K22575  AF470; fumagillin biosynthesis monooxygenase
K22598  rosB; 8-demethyl-8-aminoriboflavin-5'-phosphate synthase [EC:2.6.1.114]
K22798  auaE; anthranilate-CoA-ACP transferase [EC:6.2.1.-]
K22799  auaA; 2-methyl-4-hydroxyquinoline prenyltransferase [EC:2.5.1.-]
K22800  auaF; aurachin D monooxygenase [EC:1.14.13.-]
K22801  auaJ; aurachin B monooxygenase [EC:1.14.13.-]
K22802  auaI; aurichin B epoxide hydrolase
K23999  fom1; phosphoenolpyruvate phosphomutase / 2-hydroxyethylphosphonate cytidylyltransferase
K24000  fomD; HPP-CMP hydrolase
K25562  creE; L-aspartate N-monooxygenase (nitrosuccinate-forming)
K25563  creL, ptmB3; 3-amino-4-hydroxybenzoate 2-monooxygenase
K25594  creN; 3-amino-4-hydroxybenzoate 4-O-methyltransferase
K25597  creD; nitrosuccinate lyase
K25598  creM; 3-amino-2-hydroxy-4-methoxybenzoate diazotase
Compound
C00002  ATP
C00022  Pyruvate
C00024  Acetyl-CoA
C00025  L-Glutamate
C00026  2-Oxoglutarate
C00036  Oxaloacetate
C00049  L-Aspartate
C00061  FMN
C00062  L-Arginine
C00065  L-Serine
C00074  Phosphoenolpyruvate
C00077  L-Ornithine
C00082  L-Tyrosine
C00083  Malonyl-CoA
C00085  D-Fructose 6-phosphate
C00088  Nitrite
C00092  D-Glucose 6-phosphate
C00108  Anthranilate
C00129  Isopentenyl diphosphate
C00197  3-Phospho-D-glycerate
C00251  Chorismate
C00254  Prephenate
C00279  D-Erythrose 4-phosphate
C00353  Geranylgeranyl diphosphate
C00441  L-Aspartate 4-semialdehyde
C00448  trans,trans-Farnesyl diphosphate
C00979  O-Acetyl-L-serine
C01005  O-Phospho-L-serine
C01179  3-(4-Hydroxyphenyl)pyruvate
C01610  Puromycin
C01841  Pentalenene
C02247  Anthraniloyl-CoA
C02798  3-Phosphonopyruvate
C03167  Phosphonoacetaldehyde
C03401  L-2,3-Diaminopropanoate
C05933  N(omega)-Hydroxyarginine
C06451  2-Hydroxyethylphosphonate
C06452  (S)-2-Hydroxypropylphosphonate
C06454  Fosfomycin
C07024  3'-Keto-3'-deoxy-ATP
C07025  3'-Keto-3'-deoxy-AMP
C07026  3'-Amino-3'-deoxy-AMP
C07027  N6,N6,O-Tridemethylpuromycin-5'-phosphate
C07028  N-Acetyl-N6,N6,O-tridemethylpuromycin-5'-phosphate
C07029  N-Acetyl-N6,O-didemethylpuromycin-5'-phosphate
C07030  N-Acetyl-O-demethylpuromycin-5'-phosphate
C07031  N-Acetyl-O-demethylpuromycin
C07032  N-Acetylpuromycin
C07044  Hydroxyurea
C08057  Cycloserine
C09668  Fumagillin
C10641  Aurachin D
C12115  3-Amino-4-hydroxybenzoate
C12212  Kanosamine
C12213  Kanosamine 6-phosphate
C19814  Terpentetriene
C19815  Terpentedienyl diphosphate
C19939  Pentalen-13-al
C20397  Pentalenolactone F
C20399  Pentalenolactone D
C20400  1-Deoxy-11-oxopentalenate
C20402  Neopentalenolactone D
C20403  1-Deoxy-11beta-hydroxypentalenate
C20404  1-Deoxypentalenate
C20405  Pentalenate
C20407  Pentalenolactone
C20639  O-Ureido-L-serine
C20651  O-Ureido-D-serine
C20668  3-Dehydro-D-glucose 6-phosphate
C20940  L-Dihydroanticapsin
C20941  L-Anticapsin
C20942  Bacilysin
C20953  3-[(4R)-4-Hydroxycyclohexa-1,5-dien-1-yl]-2-oxopropanoate
C20961  N3-Fumaroyl-L-2,3-diaminopropanoate
C20962  Dapdiamide A
C20963  Dapdiamide B
C20964  Dapdiamide C
C20966  3-{[(2E)-4-Amino-4-oxobut-2-enoyl]amino}-L-alanine
C21085  3-[(1E,4R)-4-Hydroxycyclohex-2-en-1-ylidene]-2-oxopropanoate
C21086  (3E)-3-[(1R,5R,6S)-5-Hydroxy-7-oxabicyclo[4.1.0]heptan-2-ylidene]-2-oxopropanoate
C21087  3-[(1R,2S,5R,6S)-5-Hydroxy-7-oxabicyclo[4.1.0]heptan-2-yl]-2-oxopropanoate
C21093  Terpentecin
C21140  Aurachin B
C21141  4-Hydroxy-2-methyl-3-oxo-4-[(2E,6E)-farnesyl]-3,4-dihydroquinoline 1-oxide
C21330  Aurachin C
C21559  N-[(2S)-2-Amino-2-carboxyethyl]-L-glutamate
C21646  8-Amino-8-demethylriboflavin
C21647  Roseoflavin
C21648  8-Demethyl-8-(methylamino)riboflavin
C21803  8-Demethyl-8-formylriboflavin 5'-phosphate
C21804  8-Carboxy-8-demethylriboflavin 5'-phosphate
C21805  8-Amino-8-demethylriboflavin 5'-phosphate
C21873  2-Methylquinolin-4-ol
C21874  Aurachin B epoxide
C21875  Aurachin A
C22216  Cytidine 5'-{[hydroxy(2-hydroxyethyl)phosphonoyl]phosphate}
C22217  Cytidine 5'-({hydroxy[(S)-2-hydroxypropyl]phosphonoyl}phosphate)
C22388  (2S)-2-Nitrobutanedioate
C22416  Cremeomycin
C22425  3-Amino-2-hydroxy-4-methoxybenzoate
C22455  3-Amino-2,4-dihydroxybenzoate
C22617  (+)-exo-beta-Bergamotene
C22618  Fumagillol
C22619  5-Dehydrofumagillol
C22629  5-Dehydro-6-demethoxyfumagillol
C22631  5-Dehydro-6-demethoxy-6-hydroxyfumagillol
C22650  Prefumagillin
C22651  Dodecapentaenoyl-[acyl-carrier protein]
Reference
  Authors
Sandmann A, Dickschat J, Jenke-Kodama H, Kunze B, Dittmann E, Muller R
  Title
A Type II polyketide synthase from the gram-negative Bacterium Stigmatella aurantiaca is involved in Aurachin alkaloid biosynthesis.
  Journal
Angew Chem Int Ed Engl 46:2712-6 (2007)
DOI:10.1002/anie.200603513
Reference
  Authors
Vetter ND, Langill DM, Anjum S, Boisvert-Martel J, Jagdhane RC, Omene E, Zheng H, van Straaten KE, Asiamah I, Krol ES, Sanders DA, Palmer DR
  Title
A previously unrecognized kanosamine biosynthesis pathway in Bacillus subtilis.
  Journal
J Am Chem Soc 135:5970-3 (2013)
DOI:10.1021/ja4010255
Reference
  Authors
Ozcengiz G, Ogulur I
  Title
Biochemistry, genetics and regulation of bacilysin biosynthesis and its significance more than an antibiotic.
  Journal
N Biotechnol 32:612-9 (2015)
DOI:10.1016/j.nbt.2015.01.006
Reference
PMID:8576156
  Authors
Tercero JA, Espinosa JC, Lacalle RA, Jimenez A.
  Title
The biosynthetic pathway of the aminonucleoside antibiotic puromycin, as deduced from the molecular analysis of the pur cluster of Streptomyces alboniger.
  Journal
J Biol Chem 271:1579-90 (1996)
DOI:10.1074/jbc.271.3.1579
Reference
  Authors
Hollenhorst MA, Clardy J, Walsh CT
  Title
The ATP-dependent amide ligases DdaG and DdaF assemble the fumaramoyl-dipeptide scaffold of the dapdiamide antibiotics.
  Journal
Biochemistry 48:10467-72 (2009)
DOI:10.1021/bi9013165
Reference
  Authors
Schwarz J, Konjik V, Jankowitsch F, Sandhoff R, Mack M
  Title
Identification of the Key Enzyme of Roseoflavin Biosynthesis.
  Journal
Angew Chem Int Ed Engl 55:6103-6 (2016)
DOI:10.1002/anie.201600581
Reference
  Authors
Kumagai T, Koyama Y, Oda K, Noda M, Matoba Y, Sugiyama M
  Title
Molecular cloning and heterologous expression of a biosynthetic gene cluster for the antitubercular agent D-cycloserine produced by Streptomyces lavendulae.
  Journal
Antimicrob Agents Chemother 54:1132-9 (2010)
DOI:10.1128/AAC.01226-09
Reference
  Authors
Hamano Y, Kuzuyama T, Itoh N, Furihata K, Seto H, Dairi T
  Title
Functional analysis of eubacterial diterpene cyclases responsible for biosynthesis of a diterpene antibiotic, terpentecin.
  Journal
J Biol Chem 277:37098-104 (2002)
DOI:10.1074/jbc.M206382200
Reference
  Authors
Quaderer R, Omura S, Ikeda H, Cane DE
  Title
Pentalenolactone biosynthesis. Molecular cloning and assignment of biochemical function to PtlI, a cytochrome P450 of Streptomyces avermitilis.
  Journal
J Am Chem Soc 128:13036-7 (2006)
DOI:10.1021/ja0639214
Reference
PMID:7500951
  Authors
Hidaka T, Goda M, Kuzuyama T, Takei N, Hidaka M, Seto H
  Title
Cloning and nucleotide sequence of fosfomycin biosynthetic genes of Streptomyces wedmorensis.
  Journal
Mol Gen Genet 249:274-80 (1995)
DOI:10.1007/BF00290527
Reference
  Authors
Lin HC, Tsunematsu Y, Dhingra S, Xu W, Fukutomi M, Chooi YH, Cane DE, Calvo AM, Watanabe K, Tang Y
  Title
Generation of complexity in fungal terpene biosynthesis: discovery of a multifunctional cytochrome P450 in the fumagillin pathway.
  Journal
J Am Chem Soc 136:4426-36 (2014)
DOI:10.1021/ja500881e
Related
pathway
ko00010  Glycolysis / Gluconeogenesis
ko00020  Citrate cycle (TCA cycle)
ko00030  Pentose phosphate pathway
ko00220  Arginine biosynthesis
ko00250  Alanine, aspartate and glutamate metabolism
ko00260  Glycine, serine and threonine metabolism
ko00400  Phenylalanine, tyrosine and tryptophan biosynthesis
ko00440  Phosphonate and phosphinate metabolism
ko00900  Terpenoid backbone biosynthesis

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